EP1948637A1 - Process for amorphous esomeprazole - Google Patents
Process for amorphous esomeprazoleInfo
- Publication number
- EP1948637A1 EP1948637A1 EP05823638A EP05823638A EP1948637A1 EP 1948637 A1 EP1948637 A1 EP 1948637A1 EP 05823638 A EP05823638 A EP 05823638A EP 05823638 A EP05823638 A EP 05823638A EP 1948637 A1 EP1948637 A1 EP 1948637A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- esomeprazole
- amorphous
- water
- lyophilization
- omeprazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
The present invention relates to a commercially viable process for preparation of amorphous esomeprazole. Thus, amorphous esomeprazole is prepared by suspending esomeprazole in water and then subjecting the suspension to lyophilization at -70°C.
Description
PROCESS FOR AMORPHOUS ESOMEPRAZOLE
FIELD QF THE INVENTION
The present invention relates to a commercially viable process for preparation of amorphous esomeprazole.
BACKGROUND OF THE INVENTION
Omeprazole, chemically 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2- pyridinyl)methyl]sulfinyl]-1 H-benzimidazole and its therapeutic uses are disclosed in European Patent No. 5129. Omeprazole is a well-known gastric acid secretion inhibitor, and is useful as an anti ulcer agent. Omeprazole has a stereogenic center at sulfur and therefore exist as two optical isomers such as R-omeprazole and S-omeprazole (esomeprazole).
The salts of the enantiomers of omeprazole are described in WO 94/27988. PCT Publication No. WO 98/28294 disclosed esomeprazole in an amorphous form, a partly crystalline form A, and a substantially crystalline form B.
PCT Publication No. WO 2004/076440 A1 described crystalline forms, Form I and Form II, of esomeprazole, and its hydrates. PCT Publication No. WO 2004/020436 A1 described amorphous hydrates of esomeprazole magnesium and process for their preparation. PCT Publication No. WO 2004/002982 A2 described amorphous form of esomeprazole free base and process for its preparation.
U.S. Patent No. 6,369,085 described crystalline forms of esomeprazole magnesium, esomeprazole magnesium dihydrate, esomeprazole magnesium trihydrate and esomeprazole potassium.
The alkaline salts of (S)-enantiomer of omeprazole (esomeprazole), the pharmaceutical preparations of these salts and the method of treatment of gastric acid-related diseases using them are disclosed in US 4,738,974, US 5,877,192 and US 5,714,504. PCT Application No. PCT/IN05/00197 describes an amorphous form of esomeprazole. Even though the process described in the patent application yields amorphous esomeprazole in Laboratory scale, we have found that there is a problem in the scale up of process. The main problem in the scale up of this
process is that the development of color in the product during drying even under reduced pressure of wet product obtained.
The object of the present invention is to provide commercially viable process for pure amorphous esomeprazole. DETAILED DESCRIPTION OF THE INVENTION
In accordance with the present invention, there is provided a process for amorphous form of esomeprazole.
In accordance with the present invention, a process is provided for the preparation of amorphous esomeprazole, which comprises: a) suspending esomeprazole in water; and b) subjecting the suspension obtained in step-(a) to lyophilization to remove water.
Lyophilization is preferably carried out at about -200C to -800C and more preferably at about -400C to -700C. The esomeprazole used in the process may be in any polymorphic form, hydrated form etc., can be prepared by known techniques.
The invention will now be further described by the following examples, which are illustrative rather than limiting.
Example 1
Esomeprazole (50 gm) was suspended in water (100 ml) at 250C and then stirred at the same temperature for 3 hours. Subsequently, the water was removed by lyophilization at about -700C. After isolation from the lyophilization vessel there were obtained 49.7 gm of amorphous esomeprazole (HPLC Purity:
99.89%, water content: 2.0%).
Example 2
■ Tetrahydrofuran (250 ml) and water (500 ml) were added to esomeprazole potassium salt (50 gm) at 25 - 3O0C, cooled to 200C and then the pH is adjusted to 7.5 - 8.0 with acetic acid. The reaction mass was cooled to 50C, stirred for 2 hours at 0 - 50C, filtered the mass, washed with 50 ml of chilled mixture of water and tetrahydrofuran (2 : 1 ) and again washed with water (100 ml). To the wet cake obtained was added water (100 ml) at 250C and then
stirred for 30 minutes. Subsequently, the water was removed by lyophilization at about -600C. After isolation from the lyophilization vessel there were obtained 26.2 gm of amorphous esomeprazole (HPLC Purity: 99.87%, water content: 2.5%).
Claims
1. A process for preparation of amorphous esomeprazole, which comprises: a) suspending esomeprazole in water; and b) subjecting the suspension obtained in step-(a) to lyophilization.
2. The process as claimed in claim 1 , wherein the lyophilization is carried out at
-200C to -800C.
3. The process as claimed in claim 2, wherein the lyophilization is carried out at -400C to -700C.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IN2005/000367 WO2007054951A1 (en) | 2005-11-14 | 2005-11-14 | Process for amorphous esomeprazole |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1948637A1 true EP1948637A1 (en) | 2008-07-30 |
EP1948637A4 EP1948637A4 (en) | 2010-09-08 |
Family
ID=38023006
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05823638A Withdrawn EP1948637A4 (en) | 2005-11-14 | 2005-11-14 | Process for amorphous esomeprazole |
Country Status (3)
Country | Link |
---|---|
US (1) | US20090082572A1 (en) |
EP (1) | EP1948637A4 (en) |
WO (1) | WO2007054951A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2195309A4 (en) * | 2007-10-08 | 2013-04-24 | Hetero Drugs Ltd | Polymorphs of esomeprazole salts |
CN104133012B (en) * | 2014-07-02 | 2020-01-07 | 北京万全德众医药生物技术有限公司 | Method for measuring asenapine maleate racemate by high performance liquid chromatography |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004002982A2 (en) * | 2002-06-27 | 2004-01-08 | Dr. Reddy's Laboratories Limited | A process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof |
WO2005105054A1 (en) * | 2004-04-15 | 2005-11-10 | Dr. Reddy's Laboratories Ltd. | Dosage form having polymorphic stability |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE510666C2 (en) * | 1996-12-20 | 1999-06-14 | Astra Ab | New Crystal Modifications |
JP4681808B2 (en) * | 2001-08-03 | 2011-05-11 | チバ ホールディング インコーポレーテッド | Crystal form |
EA200500673A1 (en) * | 2002-10-22 | 2005-12-29 | Рэнбакси Лабораториз Лимитед | AMORPHIC FORM OF SALT EZOMEPRAZOL, METHOD FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITION ON ITS BASIS |
-
2005
- 2005-11-14 US US11/718,273 patent/US20090082572A1/en not_active Abandoned
- 2005-11-14 EP EP05823638A patent/EP1948637A4/en not_active Withdrawn
- 2005-11-14 WO PCT/IN2005/000367 patent/WO2007054951A1/en active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004002982A2 (en) * | 2002-06-27 | 2004-01-08 | Dr. Reddy's Laboratories Limited | A process for preparation of optically pure or optically enriched sulfoxide compounds, including amorphous esomeprazole and salts thereof |
WO2005105054A1 (en) * | 2004-04-15 | 2005-11-10 | Dr. Reddy's Laboratories Ltd. | Dosage form having polymorphic stability |
Non-Patent Citations (1)
Title |
---|
See also references of WO2007054951A1 * |
Also Published As
Publication number | Publication date |
---|---|
EP1948637A4 (en) | 2010-09-08 |
WO2007054951A1 (en) | 2007-05-18 |
US20090082572A1 (en) | 2009-03-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
17P | Request for examination filed |
Effective date: 20071128 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI SK TR |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20100810 |
|
17Q | First examination report despatched |
Effective date: 20110614 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 20111228 |
|
DAX | Request for extension of the european patent (deleted) |